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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 484213Generated: October 29, 2026

Acetonitrile → 7-(1-tert-Butoxycarbonylamino-3-azabicyclo[4.1.0]-hept-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester

https://huagongshe.com/reaction/484213

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetonitrileHCID 6342—
Reactant7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 10546084—
Reactanttert-Butyl 3-azabicyclo[4.1.0]heptan-1-ylcarbamateHCID 20089946—
Product7-(1-tert-Butoxycarbonylamino-3-azabicyclo[4.1.0]-hept-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl esterHCID 8674634288%

Reaction Steps

A solution of 1-tert-butoxycarbonylamino-3-azabicyclo-[4.1.0]heptane (200 mg, 0.94 mmol) and the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (327 mg, 0.85 mmol) in acetonitrile (12 ml) was heated at reflux for 3 hours. Solvent was removed in vacuo, and the residue was chromatographed on silica gel (eluant: 50% ethyl acetate/hexane) to afford the title product as an off-white solid (423 mg, 0.758 mmol, 88% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05229396
Source datasetuspto-grants-1993_07
ORD IDord-ddaa2b9351c943b2b235ec49f5dab504
Source noteuspto-grants-1993_07